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Pet Friendly Holiday Rentals in Berkshires

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    ₹15,960
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    ₹28,728
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    5 of 5 stars (8) Excellent
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    ₹8,874
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    5 of 5 stars (9) Excellent
    Becket
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    ₹108,529
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    4.5 of 5 stars (3) Very good
    Overview Reviews (3)
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    ₹28,728
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    About this property
    handsome and welcoming, this authentic Berkshire lodge will make you feel like you`re in an old fashioned Christmas card! fireplace blazing, wood floors post and beam, hand planed planks. in the kitchen the floor is marble slabs from the famous lee marble quarry. Daniel Chester French, the designer... View all property information
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    5 of 5 stars Reviewed 12 June 2014
    I had several summer months here, it never disappoints. Full of nature's bounty, hospitable host, friendly vacationers. Very close to all the best of the Berkshires, Tanglewood...
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    ₹8,299
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    • Mountain Views
    • Safe
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    About this property
    I have a 2 to 3 bedroom first floor apartment located in a dead end street. This spacious 8 room apartment is surrounded by woods and minutes from downtown North Adams or Williamstown!! It is also walking distance to Mass MoCa!!! Animals are welcome is needed. . The master bedroom has an... View all property information
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    5 of 5 stars Reviewed 7 July 2014
    Stephanie was helpful and accommodating of us and our last minute request . Sheafs it easy to stay, come and go and we found the location convenient yet private and remote from...
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    ₹12,768
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    5 of 5 stars (1) Excellent
    Overview Reviews (1)
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    • Mountain Views
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    • x
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    • x
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    About this property
    The Writer's Room is at the top of the stairs on the right. This handsome room is made completely of wood. Ceilings are higher and there's a sitting area in the big dormer. dormer faces east and get the morning sun! The floors are wide plank cherry milled from the property. the walls are pine.... View all property information
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    5 of 5 stars Reviewed 17 June 2014
    We have taken the Writer's Room each Summer for about three years now. We find the Lodge to be authentic New England... our natural wood room to the rest of the house. It is...
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    5 of 5 stars (1) Excellent
    Becket
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Suitable for children
    • x
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    About this property
    Come to the Berkshires and stay in one of the most beloved areas of Massachusetts. We are located close to Lenox, Stockbridge, Lee, Great Barrington and more. Our 3400 square foot ranch home is located in the heart of the Berkshires awaiting memorable times with your family and friends. Our... View all property information
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    5 of 5 stars Reviewed 30 August 2014
    This was our first trip to the Berkshires and we feel fortunate to have found this fabulous home. It suited our needs perfectly as we were traveling with kids and grandparents...
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    ₹7,661
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    5 of 5 stars (108) Excellent
    Overview Reviews (108)
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    • Mountain Views
    • Satellite TV
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    • Pets allowed
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    • Suitable for children
    • x
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    • ?
    About this property
    Discover Cavalier Cottage B&B, a pet-friendly home away from your home and an attractive alternative to conventional hotels, motels and B&B's. We warmly welcome visitors who come to this beautiful and diverse area of Western Massachusetts with or without their companion animals. Since opening... View all property information
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    5 of 5 stars Reviewed 30 March 2015
    Beyond all expectations, we relaxed in royal blue, in quiet and comfortable surroundings -- a place to which we plan to return again, to enjoy in other seasons, to fully...
    5 of 5 stars Reviewed 24 March 2015
    This cottage is a great place to stay, especially for those traveling with pets. Pat is very hospitable and there is plenty of privacy. We definitely need more people & places...
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    ₹6,384
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    • Suitable for children
    • ?
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    • Elder access
    • x
    About this property
    A Fully-Furnished Extended Stay property in the Berkshires. Located across the street from the Colonial Theatre and within minutes of most Berkshire County attractions. Each spacious, efficiency (condo-style) single bedroom apartment includes living room, kitchen with full size appliances,... View all property information
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    5 of 5 stars Reviewed 3 July 2013
    WOW, this place was very nice! What you get is a place with a five minute walk from downtown, well kept buidlings and grounds, excellent floor plans, new furniture, modern...
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    ₹20,748
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    • Air Conditioning
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    • Mountain Views
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • x
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    About this property
    Enjoy all the Berkshires has to offer in our new (2014) restoration and outstanding renovation of the historic South Lee Schoolhouse. Perched on a hillside just across the road from the Housatonic River and Beartown State Forest in the hamlet of South Lee, just outside of Stockbridge, the 1892... View all property information
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    5 of 5 stars Reviewed 19 April 2015
    This is a very special place to stay in the Berkshires! Not only is its location perfect for getting to Tanglewood, Jacobs Pillow, Stockbridge, and most other Berkshires...
    5 of 5 stars Reviewed 17 April 2015
    Friends and I gathered for two days at this rental. It was everything that we could have desired and more: great location, nearby walks, a roomy and perfectly maintained rental...
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    ₹6,320
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    • Air Conditioning
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    • Mountain Views
    • Safe
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
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    • Elder access
    • x
    About this property
    The Cottage, in picturesque Stockbridge, has the PERFECT location -- minutes from Main Street Lenox, Main Street Stockbridge, The Norman Rockwell Museum, Berkshire Botanical Gardens, Tanglewood Music Festival, The Shrine of the Divine Mercy at the Congregation of Marians, shops, theaters, hiking... View all property information
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    5 of 5 stars Reviewed 5 November 2014
    Beautiful grounds, quiet, clean. Owner is available at all times. Close to all area attractions. Great Barrington, Stockbridge, West Stockbridge, Lennox are all within a 10 min...
    5 of 5 stars Reviewed 20 July 2014
    Stayed one night for weekend to Tanglewood festival. At first, it was a bit hard to find the house number accessing from north, but very close to the campus. Followed Carole's...
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    ₹9,576
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    • Air Conditioning
    • Balcony
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    • Hot Tub
    • Internet Access
    • Mountain Views
    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    Charming house with the feeling of a cottage, set on a knoll with adjacent cathedral-like pine forest. ** Stone fireplace, woodstove, beautiful kitchen with modern appliances (gas stove, microwave, refrigerator with water/ice dispenser, dishwasher, breadmaker, crockpot, blender, etc.) **... View all property information
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    ₹9,576
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    • Air Conditioning
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    • Internet Access
    • Mountain Views
    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
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    • Elder access
    • x
    • ?
    About this property
    House is very private and located on 4 acres of Land. Back yard is peaceful and overlooks ponds. The backyard has a patio/picnic area with gas grill and firepit. One of the ponds has a spurting and lighted fountain that is relaxing ...so have a campfire at night and watch the lighted fountain for a... View all property information
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    5 of 5 stars Reviewed 30 November 2014
    The photos speak for themselves. Overall, the home was a great escape from city life, and included its own scenery and lake. My only complaint is that our stay was so short-lived...
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    ₹15,960
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    5 of 5 stars (13) Excellent
    Overview Reviews (13)
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    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Mountain Views
    • Satellite TV
    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    About this property
    Quaint, , 2 story 1850's farmhouse in the Berkshires with original ceiling beams and 16' floor boards in much of the house. Fully furnished with 5 bedrooms, 2 full baths and a gorgeous screened-in porch overlooking 4 acres of gardens, stream and wooded mountains. Country kitchen with dish washer,... View all property information
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    5 of 5 stars Reviewed 20 April 2015
    We spent 3 nights here, 2 with sons, daughters in law and four grandchildren. There were plenty of bedroom plus a foldout couch, and the kitchen was very well equipped. One of...
    5 of 5 stars Reviewed 24 February 2015
    We just spent a wonderful week staying at the Berkshire Farmhouse. The house was exactly as pictured, and Elaine was a warm and friendly host. She gave us a lot of great...
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    ₹33,516
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    • Air Conditioning
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    • Hot Tub
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
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    About this property
    Enjoy your vacation in a beautiful historic house located in the heart of the Berkshires. Located two and a quarter hours north of New York City, this circa-1770s center chimney colonial will charm and delight your family and guests. 88 acres of land with views of Mt. Washington and Mount Everett... View all property information
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    ₹31,920
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    • Air Conditioning
    • Dishwasher
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    • Fireplace
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    • Hot Tub
    • Internet Access
    • Mountain Views
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    A home for the family: SKIING, SNOWSHOEING, AND SLEDDING. Fall and Winter availability. Behind the house, on the property is a HUGE hill that is great for sledding. 12 mins to Butternut. 25 mins to Jiminy. Across the road is a park that is great fun to hike, snowshoe, CC ski, and explore. A... View all property information
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    ₹3,192
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    1 / 6
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    About this property
    We rent our house for a full winter season from November through March. You can enjoy all holidays, school breaks, weekends during the winter in your own winter wonderland. Contact us for all details. Walk to charming 200 year old Monterey with library, playground, playing fields, ice skating... View all property information
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    ₹14,364
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    • Balcony
    • Internet Access
    • Mountain Views
    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Charming, One Bedroom Cottage, former sculpting studio on the Santarella Estate in Tyringham, MA. Known as the 'Silo Studio', there is a bedroom with queen bed upstairs, sitting room, wet bar with Micro/Fridge and bath downstairs. Fall asleep to sounds of babbling brook and views to pond and forest... View all property information
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    ₹14,683
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    1 / 14
    Great Barrington
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Fireplace
    • Internet Access
    • Mountain Views
    • Wi-Fi
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
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    • Elder access
    • x
    • x
    About this property
    One bedroom, one bathroom cottage on beautiful country road. Private garden and screened-in porch. Two miles to shops and restaurants of downtown Great Barrington. Enjoy nearby skiing, cycling, fishing, hiking and golf. The Space: Quaint cottage with wood burning stove. Ideal base for enjoying... View all property information
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    ₹12,768
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    • Air Conditioning
    • Fireplace
    • Grill
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    • Mountain Views
    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
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    • Elder access
    • x
    About this property
    cute cozy cottage, screened porch with views, close to everything, sleeps 4 . nice yard with big old trees and soft grass. gas bbq, just one mile to stockbridge center , Berkshire theatre festival. 5 miles to tanglewood, lenox , kripalu. 10 minutes to great barrington. bath has shower. full... View all property information
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    ₹28,728
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    • Air Conditioning
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    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • x
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    About this property
    Newly furnished 3 bedroom (with AC) & 2 1/2 bath single family home with stunning deck and in ground pool nestled in the quiet countryside opposite a horse farm. Situated minutes from West Stockbridge convenience stores and restaurants. Property is on 2 quiet tree lined acres with an enclosed... View all property information
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    1 / 19
    Great Barrington
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Mountain Views
    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
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    • Elder access
    • x
    About this property
    Surrounded by one of the most beautiful gardens in the Berkshires, Maya's Garden House is an outstanding example of an 18th century barn converted into a modern, comfortable, semi-secluded home. Located less than a mile from Great Barrington, it is close to everything the Berkshires are famous for;... View all property information
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    ₹11,172
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    1 / 12
    Windsor
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Pets allowed
    • Smoking allowed
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    • x
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    • x
    About this property
    Peaceful, mountain hideaway. Rural, yet easily accessible to all major Berkshire County and Pioneer Valley attractions. Recently renovated, this charming 2-bedroom cottage can comfortably accommodate 4-6 people or could be a romantic retreat for two. Full kitchen with all appliances gives you... View all property information
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    ₹105,337
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    1 / 10
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • x
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    About this property
    Enjoy the Fall in our New England farmhouse! Cross country ski at Canterbury Farms, only 5 minutes away! Beautifully restored Colonial historical farmhouse (1790) with almost 2 acres of lawn for playing croquet and hanging out in the sun. There is a small pond (unfenced) for frogs and birds.... View all property information
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    1 / 7
    Lee
    1 Bedroom, 1 Bathroom, Sleeps 6 | Quick View
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • x
    • x
    About this property
    sleeps 4 can combine with writer's room for large suite, private entrance. fireplace or windowed woodstove, ceiling fans cathedral ceiling, terrace with seating, pasture and forest views. windows line both sides of room and feels like a treehouse. beautiful wood floors and soft carpets make you... View all property information
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    ₹12,002
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    • Dishwasher
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    • Mountain Views
    • Private Fishing...
    • Safe
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    • Pets allowed
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    • Suitable for children
    • ?
    • ?
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    • Elder access
    • ?
    About this property
    Located in a wooded area overlooking a pristine lake, this woodsy style contemporary is a sportsman's paradise. It's a short drive to skiing (Jiminy Peak, Butternut, Catamount) and cultural attractions, (Tanglewood, National Music Center, Aston Magna, etc.) or you can fish, swim, boat, hike, or... View all property information
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    ₹19,152
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    1 / 9
    Housatonic
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Dishwasher
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    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    This house is a perfect family retreat in the Berkshires. Nestled in the Village of Housatonic you will be centrally located to all Berkshire attractions. Less that ten minutes from skiing and Tanglewood, as well as the shops and restaurants of Stockbridge, Lenox, and Great Barrington, this is... View all property information
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    ₹15,960
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    1 / 21
    Overview
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    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Mountain Views
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
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    • Elder access
    • x
    About this property
    This is a beautiful Berkshire, post and beam private house nestled in the woods just off the Appalachian trail. Set on one of the Berkshires most coveted roads close to fresh water swimming in Lake Garfield, boating, fishing, classical outdoor concerts at Tanglewood & Skiing are all close by. The... View all property information
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    1 / 14
    Lenox
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • x
    About this property
    This summer cottage built in the 1950's has recently been completely renovated from stem to stern to bring it up to date with the most current design standards. It is a 2-bedroom, 1-bathroom space with a beautiful backyard for grilling. There is also an amazing dining room surrounded by windows... View all property information
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    ₹19,152
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    • Dishwasher
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    • Mountain Views
    • Satellite TV
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    • Pets allowed
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    • Suitable for children
    • x
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    • x
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    About this property
    Secluded mountain home surrounded by 27 acres yet convenient to major attractions including Jiminy Peak, Williamstown, Hancock Shaker Village, Tanglewood, and MassMOCA. Home offers 3 bedrooms and 2 full baths with finished basement recreation room. Updated kitchen with all amenities needed for home... View all property information
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    5 of 5 stars Reviewed 12 October 2014
    Stayed here for a couple nights over labor day to get out of the city. The place is perfect for a group of 4 and even better for our 2 dogs. Great little creek for them to go...
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